3-azabicyclo[3.3.1]nonane → HCID 10474387, compound

HRID 1944528Notes

Reaction equation

HRID 1944528 reaction equation
F[C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][C:9]2[CH:10]=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:7])=[CH:4][CH:3]=1.[CH:21]12[CH2:29][CH:25]([CH2:26][CH2:27][CH2:28]1)[CH2:24][NH:23][CH2:22]2.C(N(CC)C(C)C)(C)C>CS(C)=O>[CH:21]12[CH2:29][CH:25]([CH2:26][CH2:27][CH2:28]1)[CH2:24][N:23]([C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][C:9]3[CH:10]=[N:11][C:12]4[C:17]([CH:18]=3)=[CH:16][CH:15]=[CH:14][CH:13]=4)=[O:7])=[CH:4][CH:3]=1)[CH2:22]2

Participants

5

Reactant 3

HCID 426033-azabicyclo[3.3.1]nonaneHCID 81531DiisopropylethylamineHCID 18146450HCID 18146450, compound

Product 1

HCID 10474387HCID 10474387, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 4-fluoro-N-quinolin-3-yl-benzamide (0.080 g, 0.299 mmol), 3-aza-bicyclo[3.3.1]nonane (0.200 g, 1.60 mmol) and N,N-diisopropylethylamine (0.10 mL, 0.57 mmol) in dimethyl sulfoxide (2 mL) was heated to 100° C. for 11 days. The DMSO solution was applied to a preparative reverse phase C18 column, and the product was eluted with a gradient of acetonitrile in water with 0.1% trifluoroacetic acid, to give the product as a trifluoroacetate salt, a yellow solid, 0.065 g (36%). MS: m/z 372 (MH+). 1H NMR (DMSO-d6): 1.40-1.50 (m, 1 H), 1.58-1.93 (m, 7 H), 2.05 (br s, 2 H), 3.04-3.08 (m, 2 H), 3.85 (d, 2 H), 7.00 (d, 2 H), 7.62-7.76 (m, 2 H), 7.96 (d, 2 H), 8.02 (d, 2 H), 8.95 (d, 1 H), 9.28 (d, 1 H) and 10.45 (s, 1 H).

Workup

  1. washthe product was eluted with a gradient of acetonitrile in water with 0.1% trifluoroacetic acid

Sources & evidence

ORD record
ord-54dd711b917444e5bffd48298e33fe01
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

Loading…